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Puerto Rico Cruises Starting In October 2026, 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in October 2026, 2027 or 2028, we have 29 unique cruise itineraries and 141 departures available, operated by eight of the world's leading cruise lines departing in October.
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29 Cruises (141 Departures)
29 Cruises (141 Departures)
Departures
Duration
8 Days
19 Days
Countries Visited
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Price
$800pp
$28,480pp
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13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (2)

13 Days (12 Nights) Barcelona to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visits: Spain, Morocco, Puerto Rico
Inside
$1,778
Oceanview
$2,031
Balcony
$2,031
Suite
$6,835
From (Per Person)
A$1,778
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,284
Oceanview
$1,432
Balcony
$1,789
Suite
$6,669
From (Per Person)
A$1,284
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,264
Oceanview
$1,373
Balcony
$1,779
Suite
-
From (Per Person)
A$1,264
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$825
Oceanview
$946
Balcony
$1,085
Suite
$1,716
From (Per Person)
A$825
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,670
Oceanview
$1,888
Balcony
$2,175
Suite
-
From (Per Person)
A$1,670
Per Person
View Trip
14 Day West Indies to Spain with Viking Cruises
Cruise

14 Days (13 Nights) Barcelona to San Juan
Cruise Line: Viking
Ships: Viking Sea, Viking Sky
Departures: Oct 2026 to Nov 2028
Visits: Spain, Portugal, Sint Maarten, Puerto Rico
Exclusive Savings
Balcony
$5,238
Suite
$8,472
From (Per Person)
A$5,238
Save 1,369
Per Person
View Trip
10 Day New York to San Juan with Crystal Cruises
New ReleaseCruise

10 Days (9 Nights) New York to San Juan
Cruise Line: Crystal
Ship: Crystal Symphony
Departure: 26 October 2026
Visits: USA, Bermuda, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$5,540
Balcony
$6,840
Suite
$7,445
From (Per Person)
A$5,540
Save 1,160
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: Aug 2026 to Oct 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,899
Oceanview
$2,041
Balcony
$2,113
Suite
$4,472
From (Per Person)
A$1,899
Save 1,121
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,659
Oceanview
$2,072
Balcony
$1,816
Suite
$5,867
From (Per Person)
A$1,946
Save 596
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Sep 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,607
Suite
$2,755
From (Per Person)
A$865
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,229
Oceanview
$1,527
Balcony
$2,141
Suite
$4,575
From (Per Person)
A$1,229
Save 769
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Aug 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,051
Oceanview
$1,289
Balcony
$1,586
Suite
$2,309
From (Per Person)
A$1,051
Save 23
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,490
Oceanview
$1,568
Balcony
$1,532
Suite
$5,016
From (Per Person)
A$1,735
Save 573
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: Jun 2027 to Oct 2027
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,555
Oceanview
$1,650
Balcony
$1,746
Suite
$3,961
From (Per Person)
A$1,819
Save 735
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Aug 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,841
Oceanview
$2,176
Balcony
$2,275
Suite
$3,798
From (Per Person)
A$2,014
Save 193
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visits: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,562
Oceanview
$2,869
Balcony
$3,413
Suite
$5,779
From (Per Person)
A$2,562
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (4)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,452
Oceanview
$2,749
Balcony
$3,597
Suite
$6,138
From (Per Person)
A$2,452
Save 157
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$935
Oceanview
-
Balcony
$965
Suite
$1,638
From (Per Person)
A$935
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$2,058
Oceanview
$2,067
Balcony
$2,394
Suite
$10,658
From (Per Person)
A$2,058
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,101
Oceanview
$1,144
Balcony
$1,834
Suite
$2,319
From (Per Person)
A$1,276
Save 622
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
$2,028
Balcony
$2,344
Suite
$10,156
From (Per Person)
A$2,028
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,225
Suite
-
From (Per Person)
A$2,225
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,853
Oceanview
$2,164
Balcony
$2,268
Suite
$6,099
From (Per Person)
A$1,853
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,053
Oceanview
$1,094
Balcony
$1,598
Suite
$2,629
From (Per Person)
A$1,505
Save 185
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,661
Oceanview
$1,734
Balcony
$2,078
Suite
$6,287
From (Per Person)
A$1,661
Save 822
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Aug 2026 to Oct 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,468
Oceanview
$1,707
Balcony
$1,702
Suite
$4,176
From (Per Person)
A$1,468
Save 655
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,143
Oceanview
$1,311
Balcony
$1,529
Suite
$2,083
From (Per Person)
A$1,143
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Sep 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$1,509
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$1,509
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,129
Oceanview
$1,295
Balcony
$2,240
Suite
$3,430
From (Per Person)
A$1,310
Save 487
Per Person
View Trip
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